t-3,t-5-Dimethyl-r-2,c-6-diphenyl­piperidin-4-one

Balamurugan, S.; Thiruvalluvar, A.; Manimekalai, A.; Jayabharathi, J.

doi:10.1107/S1600536807034010

t-3,t-5-Dimethyl-r-2,c-6-diphenylpiperidin-4-one

S. Balamurugan, A. Thiruvalluvar, A. Manimekalai and J. Jayabharathi

In the title molecule, C₁₉H₂₁NO, the piperidine ring adopts a chair conformation. Two phenyl rings and two methyl groups, attached to the piperidine ring at positions 2, 6, 3 and 5, respectively, occupy equatorial positions. The dihedral angle between the two phenyl rings is 57.1 (1)°. Molecules are linked by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034010/is2193sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034010/is2193Isup2.hkl Contains datablock I

CCDC reference: 657770

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.127
Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.854     0.987
            Tmin(prime) and Tmax expected:      0.978     0.987
            RR(prime) =      0.873
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C63    -   C64     ..       6.55 su

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The conformation of the title compound was established by NMR spectroscopy by Hasan et al. (1985). Crystal structures of di-2-furylpiperidin-4-one derivatives have been reported, wherein the piperidine ring adopts a chair (Balamurugan et al., 2006), a twist-boat (Balamurugan et al., 2007) and a chair conformation (Thiruvalluvar, Balamurugan, Jayabharathi & Manimekalai, 2007). Thiruvalluvar, Balamurugan, Jayabharathi, Manimekalai & Rajarajan (2007) have reported the crystal structure of diphenylpiperidin-4-ol derivative, wherein the piperidine ring adopts a chair conformation.

In the title molecule, C₁₉H₂₁NO, the piperidine ring adopts a chair conformation (Fig. 1). Two phenyl rings and two methyl groups attached to the piperidine ring at the positions 2, 6, 3 and 5, respectively, have equatorial orientations. The dihedral angle between the two phenyl rings is 57.1 (1)°. Molecules are linked by an N1—H1···O4 (-1 + x, y, z) hydrogen bond (Fig. 2).

Related literature top

For related literature, see: Noller & Baliah (1948); Hasan et al. (1985); Balamurugan et al. (2006, 2007); Thiruvalluvar, Balamurugan, Jayabharathi, Manimekalai & Rajarajan (2007); Thiruvalluvar, Balamurugan, Jayabharathi & Manimekalai (2007).

Experimental top

The title compound was prepared by the known procedure (Noller & Baliah, 1948) and characterized using NMR techniques (Hasan et al., 1985).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT-NT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The molecular packing of the title compound, viewed down the b axis, showing the hydrogen bonds (dashed lines).

t-3,t-5-Dimethyl-r-2,c-6-diphenylpiperidin-4-one top

Crystal data top

C₁₉H₂₁NO	Z = 2
M_r = 279.37	F(000) = 300
Triclinic, P1	D_x = 1.184 Mg m⁻³
Hall symbol: -P 1	Melting point: 405(1) K
a = 7.1392 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5811 (5) Å	Cell parameters from 10924 reflections
c = 11.6276 (5) Å	θ = 1.9–27.8°
α = 102.320 (2)°	µ = 0.07 mm⁻¹
β = 107.613 (2)°	T = 298 K
γ = 101.735 (2)°	Block, yellow
V = 783.31 (6) Å³	0.30 × 0.22 × 0.18 mm

Data collection top

Bruker SMART APEXII diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2507 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 27.8°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→9
T_min = 0.854, T_max = 0.987	k = −13→13
17560 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0551P)² + 0.1535P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₂₁NO	γ = 101.735 (2)°
M_r = 279.37	V = 783.31 (6) Å³
Triclinic, P1	Z = 2
a = 7.1392 (3) Å	Mo Kα radiation
b = 10.5811 (5) Å	µ = 0.07 mm⁻¹
c = 11.6276 (5) Å	T = 298 K
α = 102.320 (2)°	0.30 × 0.22 × 0.18 mm
β = 107.613 (2)°

Data collection top

Bruker SMART APEXII diffractometer	3606 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2507 reflections with I > 2σ(I)
T_min = 0.854, T_max = 0.987	R_int = 0.022
17560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.18 e Å⁻³
3606 reflections	Δρ_min = −0.15 e Å⁻³
194 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.43830 (15)	0.75505 (11)	0.24410 (10)	0.0382 (3)
H1	0.331 (3)	0.7840 (16)	0.2495 (14)	0.058 (4)*
C2	0.49854 (18)	0.79381 (13)	0.14409 (12)	0.0377 (3)
H2	0.5555	0.8923	0.1702	0.045*
C3	0.6675 (2)	0.72851 (15)	0.12688 (13)	0.0452 (3)
H3	0.6095	0.6303	0.1032	0.054*
C4	0.8407 (2)	0.77112 (15)	0.25275 (14)	0.0478 (3)
O4	1.01600 (16)	0.82417 (15)	0.26561 (12)	0.0783 (4)
C5	0.78155 (19)	0.74549 (15)	0.36128 (13)	0.0469 (3)
H5	0.7275	0.6475	0.3422	0.056*
C6	0.60440 (18)	0.80756 (13)	0.36724 (12)	0.0390 (3)
H6	0.6554	0.9058	0.3869	0.047*
C21	0.31407 (18)	0.75191 (13)	0.02317 (12)	0.0385 (3)
C22	0.2010 (2)	0.61779 (15)	−0.03430 (14)	0.0500 (3)
H22	0.2367	0.5525	0.0031	0.060*
C23	0.0361 (2)	0.57985 (17)	−0.14633 (14)	0.0590 (4)
H23	−0.0375	0.4892	−0.1845	0.071*
C24	−0.0200 (2)	0.67568 (18)	−0.20191 (14)	0.0589 (4)
H24	−0.1312	0.6500	−0.2775	0.071*
C25	0.0882 (2)	0.80852 (17)	−0.14564 (14)	0.0564 (4)
H25	0.0501	0.8736	−0.1826	0.068*
C26	0.2547 (2)	0.84655 (15)	−0.03351 (13)	0.0464 (3)
H26	0.3276	0.9373	0.0042	0.056*
C31	0.7402 (3)	0.7603 (2)	0.02373 (16)	0.0680 (5)
H31A	0.6255	0.7314	−0.0546	0.102*
H31B	0.8396	0.7138	0.0148	0.102*
H31C	0.8016	0.8559	0.0456	0.102*
C51	0.9625 (2)	0.7943 (2)	0.48516 (16)	0.0728 (5)
H51A	0.9169	0.7753	0.5510	0.109*
H51B	1.0219	0.8899	0.5054	0.109*
H51C	1.0634	0.7487	0.4776	0.109*
C61	0.53009 (19)	0.77581 (14)	0.46923 (12)	0.0425 (3)
C62	0.5871 (2)	0.87132 (18)	0.58451 (14)	0.0602 (4)
H62	0.6657	0.9587	0.5985	0.072*
C63	0.5270 (3)	0.8370 (2)	0.67992 (15)	0.0767 (6)
H63	0.5681	0.9014	0.7578	0.092*
C64	0.4088 (3)	0.7101 (3)	0.66034 (17)	0.0745 (6)
H64	0.3681	0.6882	0.7241	0.089*
C65	0.3509 (3)	0.6158 (2)	0.54676 (17)	0.0659 (5)
H65	0.2700	0.5292	0.5330	0.079*
C66	0.4113 (2)	0.64769 (16)	0.45176 (14)	0.0511 (4)
H66	0.3713	0.5819	0.3749	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0375 (5)	0.1211 (11)	0.0795 (9)	0.0161 (6)	0.0247 (5)	0.0370 (8)
N1	0.0302 (5)	0.0506 (7)	0.0349 (6)	0.0144 (5)	0.0118 (4)	0.0120 (5)
C2	0.0337 (6)	0.0413 (7)	0.0395 (7)	0.0125 (5)	0.0138 (5)	0.0123 (5)
C3	0.0411 (7)	0.0547 (8)	0.0489 (8)	0.0204 (6)	0.0228 (6)	0.0173 (7)
C4	0.0362 (6)	0.0569 (8)	0.0603 (9)	0.0223 (6)	0.0215 (6)	0.0226 (7)
C5	0.0372 (7)	0.0601 (9)	0.0509 (8)	0.0228 (6)	0.0156 (6)	0.0232 (7)
C6	0.0324 (6)	0.0427 (7)	0.0390 (7)	0.0129 (5)	0.0089 (5)	0.0102 (6)
C21	0.0359 (6)	0.0476 (8)	0.0349 (7)	0.0128 (5)	0.0163 (5)	0.0124 (6)
C22	0.0496 (8)	0.0481 (8)	0.0492 (8)	0.0123 (6)	0.0152 (6)	0.0134 (7)
C23	0.0536 (8)	0.0592 (9)	0.0485 (9)	0.0039 (7)	0.0130 (7)	0.0040 (7)
C24	0.0473 (8)	0.0830 (12)	0.0363 (8)	0.0090 (8)	0.0094 (6)	0.0150 (8)
C25	0.0546 (8)	0.0723 (11)	0.0461 (8)	0.0194 (8)	0.0144 (7)	0.0290 (8)
C26	0.0451 (7)	0.0510 (8)	0.0436 (8)	0.0123 (6)	0.0153 (6)	0.0176 (6)
C31	0.0589 (9)	0.1070 (14)	0.0626 (10)	0.0384 (9)	0.0378 (8)	0.0371 (10)
C51	0.0436 (8)	0.1164 (15)	0.0646 (11)	0.0352 (9)	0.0114 (7)	0.0395 (10)
C61	0.0376 (6)	0.0565 (9)	0.0338 (7)	0.0231 (6)	0.0090 (5)	0.0108 (6)
C62	0.0613 (9)	0.0684 (10)	0.0442 (9)	0.0308 (8)	0.0101 (7)	0.0045 (8)
C63	0.0870 (13)	0.1156 (17)	0.0349 (9)	0.0604 (13)	0.0194 (8)	0.0113 (10)
C64	0.0760 (12)	0.1259 (18)	0.0549 (11)	0.0593 (12)	0.0361 (9)	0.0466 (12)
C65	0.0635 (10)	0.0901 (13)	0.0654 (11)	0.0327 (9)	0.0328 (8)	0.0417 (10)
C66	0.0486 (8)	0.0627 (9)	0.0454 (8)	0.0186 (7)	0.0189 (6)	0.0175 (7)

Geometric parameters (Å, º) top

O4—C4	1.212 (2)	C64—C65	1.360 (3)
N1—C2	1.4628 (17)	C65—C66	1.381 (3)
N1—C6	1.4595 (17)	C2—H2	0.9800
N1—H1	0.90 (2)	C3—H3	0.9800
C2—C3	1.549 (2)	C5—H5	0.9800
C2—C21	1.5112 (18)	C6—H6	0.9800
C3—C31	1.516 (2)	C22—H22	0.9300
C3—C4	1.507 (2)	C23—H23	0.9300
C4—C5	1.505 (2)	C24—H24	0.9300
C5—C51	1.515 (2)	C25—H25	0.9300
C5—C6	1.552 (2)	C26—H26	0.9300
C6—C61	1.5096 (19)	C31—H31A	0.9600
C21—C22	1.384 (2)	C31—H31B	0.9600
C21—C26	1.379 (2)	C31—H31C	0.9600
C22—C23	1.379 (2)	C51—H51A	0.9600
C23—C24	1.376 (3)	C51—H51B	0.9600
C24—C25	1.364 (3)	C51—H51C	0.9600
C25—C26	1.385 (2)	C62—H62	0.9300
C61—C66	1.382 (2)	C63—H63	0.9300
C61—C62	1.381 (2)	C64—H64	0.9300
C62—C63	1.394 (3)	C65—H65	0.9300
C63—C64	1.364 (4)	C66—H66	0.9300

O4···H1ⁱ	2.43 (2)	H5···H65^iv	2.6000
O4···H31B	2.6800	H6···H2	2.3600
O4···H31C	2.6800	H6···H62	2.3800
O4···H51B	2.7100	H6···H51Bⁱⁱ	2.5700
O4···H51C	2.7000	H22···N1	2.8700
O4···H62ⁱⁱ	2.6600	H22···C3	2.9700
N1···H22	2.8700	H22···H3	2.4400
N1···H66	2.6800	H23···H66^v	2.5500
C24···C31ⁱⁱⁱ	3.599 (3)	H24···H66^v	2.4800
C31···C24ⁱ	3.599 (3)	H26···H2	2.3300
C51···C62	3.398 (3)	H26···H26^vii	2.5900
C62···C51	3.398 (3)	H31A···C21	2.6700
C65···C66^iv	3.547 (3)	H31A···H64^viii	2.5500
C66···C65^iv	3.547 (3)	H31B···O4	2.6800
C3···H22	2.9700	H31B···C23ⁱ	2.9600
C21···H31A	2.6700	H31B···C24ⁱ	2.9600
C22···H3	2.8300	H31C···O4	2.6800
C23···H31Bⁱⁱⁱ	2.9600	H51A···C61	2.6400
C24···H66^v	3.1000	H51A···C62	2.8400
C24···H31Bⁱⁱⁱ	2.9600	H51B···O4	2.7100
C61···H51A	2.6400	H51B···H6ⁱⁱ	2.5700
C62···H51A	2.8400	H51B···H51Bⁱⁱ	2.4400
C64···H51Cⁱⁱⁱ	2.8900	H51C···O4	2.7000
C65···H51Cⁱⁱⁱ	2.7400	H51C···C64ⁱ	2.8900
C66···H5	2.9100	H51C···C65ⁱ	2.7400
C66···H51Cⁱⁱⁱ	2.9700	H51C···C66ⁱ	2.9700
C66···H1	2.985 (16)	H62···H6	2.3800
H1···O4ⁱⁱⁱ	2.43 (2)	H62···O4ⁱⁱ	2.6600
H1···C66	2.985 (16)	H63···H2^vi	2.5900
H2···H6	2.3600	H64···H31A^ix	2.5500
H2···H26	2.3300	H65···H5^iv	2.6000
H2···H63^vi	2.5900	H66···N1	2.6800
H3···C22	2.8300	H66···C24^v	3.1000
H3···H22	2.4400	H66···H23^v	2.5500
H5···C66	2.9100	H66···H24^v	2.4800

C2—N1—C6	112.91 (11)	C31—C3—H3	108.00
C2—N1—H1	110.0 (10)	C4—C5—H5	107.00
C6—N1—H1	109.1 (10)	C6—C5—H5	107.00
C3—C2—C21	111.82 (11)	C51—C5—H5	107.00
N1—C2—C21	110.33 (11)	N1—C6—H6	109.00
N1—C2—C3	108.65 (11)	C5—C6—H6	109.00
C2—C3—C31	113.35 (14)	C61—C6—H6	109.00
C4—C3—C31	112.24 (14)	C21—C22—H22	120.00
C2—C3—C4	108.12 (12)	C23—C22—H22	120.00
C3—C4—C5	115.81 (13)	C22—C23—H23	120.00
O4—C4—C3	121.85 (14)	C24—C23—H23	120.00
O4—C4—C5	122.34 (14)	C23—C24—H24	120.00
C6—C5—C51	113.06 (12)	C25—C24—H24	120.00
C4—C5—C6	108.70 (12)	C24—C25—H25	120.00
C4—C5—C51	112.75 (13)	C26—C25—H25	120.00
N1—C6—C5	108.99 (11)	C21—C26—H26	119.00
N1—C6—C61	111.00 (11)	C25—C26—H26	119.00
C5—C6—C61	110.51 (11)	C3—C31—H31A	109.00
C2—C21—C22	121.10 (13)	C3—C31—H31B	109.00
C22—C21—C26	118.14 (13)	C3—C31—H31C	109.00
C2—C21—C26	120.76 (13)	H31A—C31—H31B	109.00
C21—C22—C23	120.80 (15)	H31A—C31—H31C	109.00
C22—C23—C24	120.21 (16)	H31B—C31—H31C	109.00
C23—C24—C25	119.72 (14)	C5—C51—H51A	109.00
C24—C25—C26	120.07 (16)	C5—C51—H51B	109.00
C21—C26—C25	121.05 (15)	C5—C51—H51C	109.00
C6—C61—C62	121.21 (14)	H51A—C51—H51B	109.00
C62—C61—C66	118.15 (14)	H51A—C51—H51C	109.00
C6—C61—C66	120.56 (12)	H51B—C51—H51C	109.00
C61—C62—C63	120.10 (17)	C61—C62—H62	120.00
C62—C63—C64	120.74 (16)	C63—C62—H62	120.00
C63—C64—C65	119.5 (2)	C62—C63—H63	120.00
C64—C65—C66	120.5 (2)	C64—C63—H63	120.00
C61—C66—C65	121.02 (15)	C63—C64—H64	120.00
N1—C2—H2	109.00	C65—C64—H64	120.00
C3—C2—H2	109.00	C64—C65—H65	120.00
C21—C2—H2	109.00	C66—C65—H65	120.00
C2—C3—H3	108.00	C61—C66—H66	120.00
C4—C3—H3	108.00	C65—C66—H66	119.00

C6—N1—C2—C3	64.29 (14)	C51—C5—C6—N1	179.84 (13)
C6—N1—C2—C21	−172.79 (11)	C51—C5—C6—C61	−57.92 (17)
C2—N1—C6—C5	−63.18 (14)	N1—C6—C61—C62	−136.85 (15)
C2—N1—C6—C61	174.88 (11)	N1—C6—C61—C66	46.50 (18)
N1—C2—C3—C4	−55.70 (15)	C5—C6—C61—C62	102.10 (17)
N1—C2—C3—C31	179.19 (13)	C5—C6—C61—C66	−74.55 (17)
C21—C2—C3—C4	−177.71 (12)	C2—C21—C22—C23	−178.30 (13)
C21—C2—C3—C31	57.18 (17)	C26—C21—C22—C23	1.2 (2)
N1—C2—C21—C22	−59.92 (17)	C2—C21—C26—C25	178.73 (13)
N1—C2—C21—C26	120.57 (14)	C22—C21—C26—C25	−0.8 (2)
C3—C2—C21—C22	61.12 (17)	C21—C22—C23—C24	−0.8 (2)
C3—C2—C21—C26	−118.38 (15)	C22—C23—C24—C25	0.0 (2)
C2—C3—C4—O4	−125.93 (17)	C23—C24—C25—C26	0.5 (2)
C2—C3—C4—C5	53.21 (17)	C24—C25—C26—C21	0.0 (2)
C31—C3—C4—O4	−0.2 (2)	C6—C61—C62—C63	−175.98 (17)
C31—C3—C4—C5	178.97 (14)	C66—C61—C62—C63	0.8 (3)
O4—C4—C5—C6	126.84 (17)	C6—C61—C66—C65	176.81 (16)
O4—C4—C5—C51	0.7 (2)	C62—C61—C66—C65	0.1 (3)
C3—C4—C5—C6	−52.29 (17)	C61—C62—C63—C64	−1.1 (3)
C3—C4—C5—C51	−178.47 (14)	C62—C63—C64—C65	0.7 (3)
C4—C5—C6—N1	53.83 (15)	C63—C64—C65—C66	0.2 (3)
C4—C5—C6—C61	176.07 (12)	C64—C65—C66—C61	−0.5 (3)

Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+2, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z; (vi) −x+1, −y+2, −z+1; (vii) −x+1, −y+2, −z; (viii) x, y, z−1; (ix) x, y, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱⁱⁱ	0.90 (2)	2.43 (2)	3.3109 (17)	170.2 (15)

Symmetry code: (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁NO
M_r	279.37
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.1392 (3), 10.5811 (5), 11.6276 (5)
α, β, γ (°)	102.320 (2), 107.613 (2), 101.735 (2)
V (Å³)	783.31 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.854, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17560, 3606, 2507
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.127, 1.05
No. of reflections	3606
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: APEX2 (Bruker, 2004), APEX2, SAINT-NT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).